A bird sitting on a nest of eggs.

Hiking Near Lakeville, Connecticut

Shorter Routes icon

Shorter Routes

These hikes keep it under 5 miles and climb less than 1,500 feet, making them ideal for quicker outings or lower-key days. Perfect for a morning stretch, a casual afternoon, or getting outside without committing to a big push. Don’t let the stats fool you — many still pack in great views and rewarding moments.

Lion's Head

Hike Route

Lion's Head

Views
easy
1.09 mi
+544 ft
CT State Highpoint/Tri-point Out and Back

Hike Route

CT State Highpoint/Tri-point Out and Back

Geologically Significant
moderate
3.06 mi
+1,176 ft
Sunset Rock

Hike Route

Sunset Rock

Dogs Allowed
moderate
3.66 mi
+1,161 ft
Jug End Loop Trail

Hike Route

Jug End Loop Trail

Birding
easy
2.94 mi
+345 ft
Sunset Rock

Hike Route

Sunset Rock

Historical
easy
0.06 mi
+32 ft
York Lake Loop Trail

Hike Route

York Lake Loop Trail

Birding
easy
2.27 mi
+64 ft

Other Nearby Routes

Not finding what you're looking for? These additional nearby hikes offer more ways to get outside and explore the area. With a mix of lengths, difficulty levels, and terrain, you're likely to find something that fits your plans for the day. And remember, you can always use the onX Route Builder to create your own adventure from scratch.

Rand's View Out and Back

Hike Route

Rand's View Out and Back

Fall Colors
moderate
5.25 mi
+1,323 ft
Bear Mountain

Hike Route

Bear Mountain

Birding
moderate
5.23 mi
+1,555 ft
Macedonia Ridge Trail

Hike Route

Macedonia Ridge Trail

Views
strenuous
6.39 mi
+1,788 ft
Louisa Pond Loop via White-Red-Blue Trails

Hike Route

Louisa Pond Loop via White-Red-Blue Trails

Views
moderate
5.41 mi
+1,086 ft